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Kayaking Southwest Florida

Program Number: 20927RJ
Start and End Dates:
2/11/2013 - 2/16/2013;
Duration: 5 nights
Location: Naples, Florida
Price starting at: $1,295.00 - Price may vary based on date, departure city
Program Type: Water Sports Activity Level: t (see description)
Meals: 14; 5 Breakfasts, 4 Lunches, 5 Dinners    
Meal Options: Vegetarian    

Lazy, tropical rivers flow through Southwest Florida, giving life to pristine estuaries where Spanish Moss drapes from trees, and mangrove tunnels provide shelter to a myriad of bird species and aquatic creatures. With seasoned kayaking experts, experience the beauty and history of these maze-like waterways and the outlying Barrier Islands as you paddle along the Estero and Cocohatchee rivers and Rookery Bay. Learn about the legacy of the industrious Calusa Indians, as well as the missionaries, pirates, fishermen and more who have inhabited the region during the past 2000 years. Throughout your journey, thrill in opportunities to spot alligators, dolphins, manatees and more as you explore this treasured piece of hidden Florida.


• Take a short climb to the top of an ancient Indian Mound for dramatic views of the surrounding area during an exploration of Mound Key.
• Get lost (in a good way!) in the Ten Thousand Islands and waterways of the Fakahatchee Strand Preserve.
• Glide across shallow bays and check out the coastal wildlife at Barefoot Beach Preserve.

Activity Particulars

Kayaking 5-12 miles per day.

Coordinated by Road Scholar.


Named for the Italian city and only two miles west of Picayune Strand State Forest, Naples is part of the Paradise Coast vacation area that includes Marco Island and the Everglades. The city is home to a thriving arts scene and nourished by its clean beaches and many championship golf courses.

Centrally-located hotel.
Meals and Lodgings
   Port of the Island Resort
  Naples, FL 5 nights
 Port of the Island Resort
Type: Hotel
  Description: The Port of the Islands is a very unique property located in the heart of the Everglades. Please note that the resort is located in a remote area 15 miles from Everglades City, Marco Island, and East Naples, and that there are no shops or other facilities nearby or within walking distance. While this helps to add to the exclusiveness of the program, we want to make sure that you are prepared by bringing any necessities you need with you. We will be making a trip to a local grocery store on Day 2 of the program, so you may be able to pick up any items you may have forgotten, but if you do not have your own vehicle you will not be able to travel throughout the area on your own.
  Contact info: 25000 Tamiami Trail East
Naples, FL 34114 USA
phone: 239-394-3005
  Room amenities: Complimentary light service replenishing towels Trash removal is provided to all guests on a daily basis Start up Complimentary Coffee and Toiletries are provided in your unit. Complimentary Direct TV including HBO Microwave Mini Refrigerator DVDPlayer 4 Cup Coffee maker
  Facility amenities: Heated outdoor swimming pool Picnic area/Chickee Hut Fitness Center and Locker/Shower Area Free Parking Game room with poker and pool tables Internet access in public areas Coin-operated laundry facilities "The Catch" Restaurant and Bar: Open 12 pm-l0 pm Tuesdays- Sunday (Closed Monday} Full-service marina on site Resort hours are 8:30am-5pm,daily. If returning to the property after office hours, be sure to have a room key with you to enter the building. If you arrive late and need to contact someone, please call the Road Scholar Emergency Cell phone at: 617-780-4318
  Smoking allowed: No
  Additional nights prior: Price based on availablility Call Port of the Island Resort at 239-394-3005 to book pre and post nights. Make sure to let hotel know that you are with the Road Scholar group.
  Check in time: 3:00 PM
  Additional nights after: Price based on availablility Call Port of the Island Resort at 239-394-3005 to book pre and post nights. Make sure to let hotel know that you are with the Road Scholar group.
  Check out time: 11:00 AM

Travel Details
  Start of Program:
4:00 PM in the Hotel Lobby You will be staying at Port of the Island Resort that night.
  End of Program:
12:00 PM You will be staying at Port of the Island Resort the night before.
  Required documents:
The Participant Information Form is required.
  Parking availability:
Complimentary on-site parking.
To Start of Program
  Location:  Naples, FL
  From End of Program
  Location: Naples, FL
    (Additional transportation information same as above)
Travel Details

From Southwest Florida International Airport to Port of the Islands Resort


From Airport






approx. $75.00


From Southwest Florida International Airport to Port of the Islands


From Airport




Commercial Van/Shuttle
Classic Transportation
phone: 800-553-8294
Advanced Reservations Required


Per Person/One Way:


Prices are subject to change.

Driving Directions
  From I-75 to Port of the Islands Resort Take Exit 101 for County Rd 951/FL-84 toward Naples/Marco Island. Keep right at the fork, follow signs for Rookery Bay Reserve/Edison College/Naples/Marco Island and merge onto Collier Blvd/County Rd 951. Turn Left onto FL-90 S/US-41/Tamiami Trail E. Port of the Islands will be on the right.
Equipment Requirements: Kayaks and life jackets will be provided on the program.
The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Daily Schedule

Day 1: Arrival, Check-In, and Orientation
(Monday, February 11)
 Afternoon: HOTEL CHECK-IN: Available from 4:00pm. PROGRAM REGISTRATION: After you have your room assignment, come over to the Road Scholar desk in the lobby to pick up your arrival packet containing your name tag, the up-to-date schedule, and to confirm the time of the orientation session. Please be aware that program activities and scheduled times could change due to local circumstances. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.
 Dinner: Dinner will be served in the hotel.
 Evening: ORIENTATION : We'll review the schedule and any changes; discuss responsibilities, safety guidelines, emergency procedures; and answer any questions you may have. You'll also have an opportunity to meet the program staff and your fellow participants.
Accommodations: Port of the Island Resort
Meals Included: Dinner

Day 2: Port of the Isles & Natural History
(Tuesday, February 12)
 Breakfast: Breakfast is included at the hotel
 Morning: Port of the Isles

We will explore the Port of Isles waterway and hidden canals to get aquaited with our kayaks. We will take a few detours from the waterway to explore mangrove canals. If fortune smiles on us we may spot a gentle manatee.

 Lunch: Lunch in a local restaurant or picnic
 Afternoon: LECTURE - Florida Natural History
 Dinner: Dinner at hotel
 Evening: After dinner, you will have time on your own to rest or explore the area.
Accommodations: Port of the Island Resort
Meals Included: Breakfast, Lunch, Dinner

Day 3: Wiggins Pass & Barefoot Preserve
(Wednesday, February 13)
 Breakfast: Breakfast at the hotel.
 Morning: KAYAKING: Barefoot Beach Preserve - Wiggins Pass

Barefoot Beach Preserve consists of over 300 acres on a barrier Island. It is bordered by the gulf of Mexico, sand dunes, mangroves and tidal black bays. It is one of the last stretches of undeveloped beachfront land in South Florida. This paddle brings us back in time to an area that has remained rich and unspoiled for more than a hundred years.

We put in at Cocohatchee River Park Marina. This area is mangrove estuary. From the marina, we enter a boat channel which leads us to the secluded marked paddling trail of Barefoot Beach Preserve (FL Pristine Waters). We will land the kayaks and explore the Saylor Nature Trail (variety of native vegetation and Gopher Tortoise sanctuary) or stroll along the beach. We will also paddle along the Delnor –Wiggins State Beach (barrier island).

Wildlife viewing possibilities: Coastal and wading birds, dolphins, manatee, and a variety of fish and shellfish.

 Lunch: Lunch at a local restaurant
 Afternoon: FIELD TRIP/LECTURE: Marco Island Historical Museum The new Marco Island Historical Museum will bring to life the history of Southwest Florida’s Calusa Indians, a vanished civilization that is very important to the make p of this region. An expert led lecture will unravel mysteries of the Calusa, from the unique Shell Mounds to being responsible for the untimely death of Spanish discoverer Ponce de Leon. LECTURE: Wild Florida given by a Master Naturalist
 Dinner: Enjoy dinner at a local restaurant
 Evening: After dinner, you will have time on your own to rest or explore the area.
Accommodations: Port of the Island Resort
Meals Included: Breakfast, Lunch, Dinner

Day 4: Estero River & Mound Key
(Thursday, February 14)
 Breakfast: Breakfast at the hotel.
 Morning: KAYAKING: Estero River & Bay

Explore with us the jungle-like stretches of the beautiful Estero River as we navigate its twisting and turning oxbows. Live Oaks hang lazily over the river spilling long beards of Spanish Moss toward the water’s crystal clear surface. Here, it is easy for us to imagine what Florida was like in the first days of pioneer settlement. Watch for abundant wildlife along the surrounding shores and swimming in the waters alongside the canoe.

Before we begin our paddle we will tour the Koreshan Unity, an idealistic commune established on the banks of the Estero River during the waning years of the nineteenth century. This village has now been turned into a state park. Learn how Dr. Cyrus Teed attempted to bring to life his “New Jerusalem,” founded on the principles that he received during a “divine illumination” in 1869. The settlement buildings of the Koreshan Unity have been restored to their appearance during the early years of the 20th century. Discover the intriguing reasons why this settlement is now a historic site instead of a living community.

We put in at Koreshan State Historic Site where Halfway Creek enters from the south. From this point to Estero Bay, predominant vegetation is mangrove and on higher ground some Australian and Sand pine. Passing a number of small bays and side streams, the river enters Estero Bay and tidal influence becomes quite pronounced. Wildlife viewing possibilities on river: alligators and various birds; Bay: a variety of birds as well as marine life (horseshoe crabs, stingrays, fish).

 Lunch: Box Lunch
 Afternoon: FIELD TRIP: Mound Key - Calusa “Capital”

We continue the paddle across the stunning, shallow, sun-dappled waters of Estero Bay as we examine the rich ecosystem upon which the native peoples of Southwest Florida constructed their prosperous society. See native birds, mangrove islands and rich estuarine breeding grounds on the way to a hidden alcove marking the entrance to the State archaeological treasure we call: Mound Key.

Climb with us to the top of Mound One, the highest point in Southwest Florida and legendary home of the King of the Calusa Empire. From here, witness the realm over which these talented and industrious people ruled. Descend to the ancient water court, an inner sanctum for the native Calos, here in their capital city.

Learn of the various peoples who made this 125 acre island home for the past 2000 years, from the Calusa, to the Spanish missionaries, to an aging pirate, some Cuban fisherman far from home, and members of a now-defunct utopian commune that settled on the island in the late Victorian era.

 Dinner: Dinner at a local restaurant.
 Evening: After dinner, you will have time on your own to rest or explore the area.
Accommodations: Port of the Island Resort
Meals Included: Breakfast, Lunch, Dinner

Day 5: East River, Fakahatchee, and Everglades Frontier Towns
(Friday, February 15)
 Breakfast: Breakfast at the hotel.
 Morning: FIELD TRIP/ LECTURE: Everglades City & Chokoloskee

Take a settlement at the end of the world, add a legendary gentlemen’s fishing and hunting lodge, bring in a daring financier with the determination to build a road across the Everglades, lay out an imposing city with a grid of wide boulevards and a town circle, then let it all stew for one hundred years of hurricanes, financial ruin, smugglers, intrigue and isolation and you get…Everglades City.

We will also explore the historic fishing village of Chokoloskee where you will be visiting an old Indian Trading Post – virtually unchanged since the day it was built. A lecture by a local author and historian will tell the story of this frontier town.

 Lunch: Lunch either be a picnic or held in a local restaurant.
 Afternoon: KAYAKING: East River, Wild and Scenic

The East River flows through Fakahatchee Strand State Preserve, just west of Everglades National Park. It is a beautiful and varied creek, passing through a succession of small lakes and canopied mangrove tunnels before widening into a tidal river. The mangrove tunnels are particularly beautiful, becoming larger and more majestic with each passing mile. Alligators may be seen in the river's upper section, as well as a variety of birds.

 Dinner: Farewell Dinner
Accommodations: Port of the Island Resort
Meals Included: Breakfast, Lunch, Dinner

Day 6: Program Wrap-up and Departures
(Saturday, February 16)
 Breakfast: Breakfast is included at the hotel.
 Morning: Time to say your good-byes and reflect on the week!
Meals Included: Breakfast
Important information about your itinerary: Every effort has been made to ensure the accuracy and completeness of the information featured on this website. Itineraries are based on our best information at this time. Circumstances beyond our control may require us to adjust itineraries or other details. We regret any inconvenience this may cause and appreciate your understanding. Information will be sent to you from your Program Provider approximately three weeks prior to the program start date. The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Suggested Reading List

Canoeing and Kayaking Florida (Canoe and Kayak Series)

Author: Johnny Molloy, John Pearce, Elizabeth F. Carter, Lou Glaros, Doug Sphar

Description: Completely updated, Canoeing & Kayaking Florida, 2nd is the most comprehensive guide to the best of Florida’s unique streams, springs, creeks, and rivers. Engaging and concise yet filled with carefully selected details vital to any successful Florida paddling adventure, Canoeing & Kayaking Florida spares readers encyclopedic fluff in favor of practical, no-nonsense information. With expanded regional maps and revised river maps, Canoeing & Kayaking Florida is simply the best and most informative Florida paddling guide available. Florida has a lot of sand, but it also has a lot of water—and not just for drinking. It’s only natural that native Floridians and transplants alike paddle and ply the waterways of this waterway-rich state. Of course, Florida’s native Indians and subsequent settlers used the creeks, streams, and rivers long before the first plastic kayak or fiberglass canoe took to this watery paradise. In the early 1970s, the state of Florida established a canoe trail system, which was born out of paddlers discovering the many destinations here. For various reasons, this state-sanctioned canoe trail system lost momentum.

The Swamp: The Everglades, Florida, and the Politics of Paradise

Author: Michael Grunwald

Description: The Everglades was once reviled as a liquid wasteland, and Americans dreamed of draining it. Now it is revered as a national treasure, and Americans have launched the largest environmental project in history to try to save it. The Swamp is the stunning story of the destruction and possible resurrection of the Everglades, the saga of man's abuse of nature in southern Florida and his unprecedented efforts to make amends. Michael Grunwald, a prize-winning national reporter for The Washington Post, takes readers on a riveting journey from the Ice Ages to the present, illuminating the natural, social and political history of one of America's most beguiling but least understood patches of land. The Everglades was America's last frontier, a wild country long after the West was won. Grunwald chronicles how a series of visionaries tried to drain and "reclaim" it, and how Mother Nature refused to bend to their will; in the most harrowing tale, a 1928 hurricane drowned 2,500 people in the Everglades. But the Army Corps of Engineers finally tamed the beast with levees and canals, converting half the Everglades into sprawling suburbs and sugar plantations. And though the southern Everglades was preserved as a national park, it soon deteriorated into an ecological mess. The River of Grass stopped flowing, and 90 percent of its wading birds vanished. Now America wants its swamp back. Grunwald shows how a new breed of visionaries transformed Everglades politics, producing the $8 billion rescue plan. That plan is already the blueprint for a new worldwide era of ecosystem restoration. And this book is a cautionary tale for that era. Through gripping narrative and dogged reporting, Grunwald shows how the Everglades is still threatened by the same hubris, greed and well-intentioned folly that led to its decline.

The Calusa and Their Legacy: South Florida People and Their Environments (Native Peoples, Cultures, and Places of the Southeastern United States)

Author: Darcie A Macmahon

Description: This history, rich with photographs and colorful drawings of the remarkable Calusa Indians who controlled all of south Florida when Europeans first arrived in the New World, presents a vivid picture of the luxurious natural environment that sustained the Calusa--the teeming estuaries along Florida's coasts, which have supported people for thousands of years. The Calusa were the last native Florida Indian people to succumb to colonization, but by the mid-1700s they had disappeared entirely. This book describes the artifacts they left behind and the plants and animals that inhabited the landscape and the underwater world of their ecosystem. It also discusses their traditions that survive to the present day among modern fisherfolk and the vibrant culture of Native Americans in south Florida--the Seminole and Miccosukee peoples. The strength of this book is its dual treatment of both culture and environment. The authors' premise is that culture affects every aspect of people's existence and that to understand a culture, one must first appreciate the environment in which it develops. By learning about both, modern citizens will be better equipped to make the right decisions for wise stewardship of the earth. The Calusa and Their Legacy will inspire readers to value south Florida's multicultural history and ecology. It is written for a broad audience of all ages (from elementary schoolers to senior citizens) and all educational levels. It will be enjoyed by environmentalists, eco/heritage tourists, and everyone interested in understanding a sense of place in the natural world. The book's dramatic and authentic illustrations of Calusa life were created by artists working at the Florida Museum of Natural History in Gainesville, where a major permanent exhibition has interpreted this story since 2002.

Gladesmen: Gator Hunters, Moonshiners, and Skiffers (Florida History and Culture)

Author: Glen Simmons, Laura Odgen

Description: Few people today can claim a living memory of Florida's frontier Everglades. Glen Simmons, who has hunted alligators, camped on hammock-covered islands, and poled his skiff through the mangrove swamps of the glades since the 1920s, is one who can. Together with Laura Ogden, he tells the story of backcountry life in the southern Everglades from his youth until the establishment of the Everglades National Park in 1947. During the economic bust of the late ‘20s, when many natives turned to the land to survive, Simmons began accompanying older local men into Everglades backcountry, the inhospitable prairie of soft muck and mosquitoes, of outlaws and moonshiners, that rings the southern part of the state. As Simmons recalls life in this community with humor and nostalgia, he also documents the forgotten lifestyles of south Florida gladesmen. By necessity, they understood the natural features of the Everglades ecosystem. They observed the seasonal fluctuations of wildlife, fire, and water levels. Their knowledge of the mostly unmapped labyrinth of grassy water enabled them to serve as guides for visiting naturalists and scientists. Simmons reconstructs this world, providing not only fascinating stories of individual personalities, places, and events, but an account that is accurate, both scientifically and historically, of one of the least known and longest surviving portions of the American frontier. Glen Simmons has lived in the south Florida Everglades since his birth in 1916 in Homestead. In 1995 he was awarded a State of Florida Heritage Award for his unique contribution to Florida's history and folk culture. He has demonstrated and taught glades skiff building for the Florida Department of State, Bureau of Folklife, and the South Florida Historical Society; his boats are on permanent display at the Florida Folklife Museum in White Springs, Florida, and at the Historical Museum of Southern Florida, Miami.

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